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Communication

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Green Soap: An Extraction and Saponication of Avocado Oil


Susan Sutheimer,* Jacqueline M. Caster, and Simone H. Smith
Chemistry Program, Green Mountain College, Poultney, Vermont 05764, United States
S Supporting Information
*

ABSTRACT: An introductory level green chemistry experiment is described that places a


new twist on soap-making in lab. In this experiment, oil is extracted from an avocado, after
which the oil is saponied to produce bars of green craft soap. Commonly used extraction
solvents, such as petroleum ether, methylene chloride, and hexane, are replaced with safer
ethyl acetate to extract the oil. Students nd the experiment helpful in discovering the
reality of fats and oils in foods, and in becoming aware of the direct relationship between
oils in plants and soap. This experiment has been successfully carried out by students of
introductory organic chemistry lab classes, but could be used by a general chemistry or an
advanced placement high school class.

KEYWORDS: First-Year Undergraduate/General, Second-Year Undergraduate, Organic Chemistry,


Hands-On Learning/Manipulatives, Inquiry-Based/Discovery Learning, Green Chemistry, Natural Products, Solutions/Solvents

PRE-LAB ASSIGNMENT
The introductory material for the lab experiment includes
information about elaioplastids, the cell structures of plants that
contain the oil, and explains why isopropyl alcohol is used in
conjunction with ethyl acetate to break down cell structures. It
also explains that using ethyl acetate is a safer solvent than
those used historically for extractions. However, it challenges
students to nd on their own the structures of fats, soap, and
ethyl acetate, as well as the chemical reaction for making soap,
and then to draw them by hand or by using molecular drawing
software. This inquiry-based, pre-lab exercise is meant to
reinforce the molecular theory behind the soap-making process.
Additionally, the combination of a fat extraction plus
saponication reaction during a single lab helps to exemplify
the real-world nature of soap production.

n a new twist to an old experiment, the procedure reported


herein provides an inquiry-based, real-world examination of
the process of preparing a soft, green, craft soap beginning with
the extraction of green-colored oil from an avocado using a
greener (safer) extraction solvent. As early as 1925, an article
appeared in this Journal describing the soap industry.1 By 1947,
the high school textbook Applied Chemistry listed a student
laboratory experiment on soap making.2 Several authors in this
Journal have described the soap-making process in detail for the
undergraduate and high school laboratory,36 with one
illustrating the versatility of the starting fats (solids) or oils
(liquid fats).3 All of these articles include images of chemical
structures of fats and soaps and explain the process of soap
making. Likewise, extractions using solvents are common in
introductory organic chemistry laboratories, as well as in
research and industrial laboratories. In this updated experiment,
both the oil extraction and soap-making techniques are
combined in a unique and fun way that illustrates the
connectivity between seemingly disparate industrial processes.
The experiment also encourages students to recognize the
presence of fats and oils in foods, and in becoming aware of the
direct relationship between oils in plants and soap.
The current experiment utilizes a greener solvent to extract
the oil from avocado by using the relatively less toxic solvent
ethyl acetate rather than the more commonly used chlorinated
solvents, petroleum ether, or hexane.79 Ethyl acetate is not
only regarded as a highly ecient solvent, but is also easily
degraded in the water and air compared to other solvents.10,11
Using a greener solvent emphasizes attention to the Principles
of Green Chemistry and to the toxicity to which many students
are unnecessarily subjected in some undergraduate laboratory
procedures.12
XXXX American Chemical Society and
Division of Chemical Education, Inc.

METHOD FOR SOAP MAKING


Students work in pairs; the experiment requires 4 h to
complete. An avocado is peeled, the pit is removed, and the
esh is extracted with a solution of ethyl acetate and isopropyl
alcohol. The decanted solvent containing the oil is evaporated
under the hood using a warm water bath. The oil, along with
additional solid fat (Crisco) and vegetable oil, is saponied by
mixing with aqueous NaOH. During a 2030 min mixing time,
students build molecular models of fat and soap. Bars of soap
are cured for 46 weeks, during which time the saponication
reaction continues and the pH of the soap decreases from >12
to near neutral. Complete pre-lab and step-by-step instructions
are included in the Supporting Information.

DOI: 10.1021/acs.jchemed.5b00188
J. Chem. Educ. XXXX, XXX, XXXXXX

Journal of Chemical Education

Communication

HAZARDS
Eye protection and gloves should be worn throughout this
procedure. Ethyl acetate and isopropyl alcohol are both
ammable, minimally toxic if inhaled, but are toxic if consumed.
A laboratory hood should be used for evaporation of the
solvents. Sodium hydroxide is caustic and should be handled
carefully. The newly prepared bars of soap have a high pH
(>12) due to residual NaOH, so they should not be handled for
some time after they are poured. The pH decreases to near
neutral (8) after curing for 46 weeks.

this lab and found the experiment helpful in recognizing the


presence of fats and oils in foods, and in becoming aware of the
direct relationship between oils in plants and soap. Their
comments included
Overall I really liked this lab. I was able to see how you
make natural soaps....It was fun and easy and it teaches you
the basics of organic chemistry. I never would have guessed it
could be so simple.
This lab was denitely very interesting. I never knew that
avocados contained that much fat.
This particular lab was interesting as it both helped me
understand the real synthesis aspects of soap and then view it
in real time.
I enjoyed this lab thoroughly and thought that it was
worthwhile both from an educational perspective and a
hands-on learning opportunity to produce a useful substance.
I really liked the lab! It was straight forward and easy to
follow and I cant wait to see how it comes out.

DISCUSSION
Avocado was chosen for its high fat content (14%). The
greener solvent, ethyl acetate, was a reasonable substitute for
other, more toxic solvents to extract avocado oil with 10
students reporting yields of 7.414.4% fat by weight (Figure 1).

ASSOCIATED CONTENT

S Supporting Information
*

A complete lab handout including inquiry based pre-lab


assignment, instructions, an example of student results and a
table listing the mass of avocado esh compared to avocado oil
obtained by 10 students is included. This material is available
via the Internet at http://pubs.acs.org.

AUTHOR INFORMATION

Corresponding Author

*E-mail: sutheimers@greenmtn.edu.
Notes

The authors declare no competing nancial interest.

ACKNOWLEDGMENTS
This work was supported by Green Mountain College through
an Undergraduate Research Grant.

Figure 1. Three completed bars of soap and avocado oil.

The average amount of fat obtained was about 14 3 g of


avocado oil per avocado. Isopropyl alcohol was used in
conjunction with the ethyl acetate to break down cell structures
so that the oils were more easily extracted. This oil is both a
coloring agent and a portion of the total fats used in the soapmaking process. Since the volume of avocado oil is relatively
small, additional fats are added to create approximately normalsized bars of soap. This procedure did not use a salting out
procedure that was commonly employed in lab exercises, but is
generally not used in craft soap-making.13 Rather, the soap was
allowed to cure slowly for 46 weeks, consistently crafting
three bars of a mild soap. Finally, because students complained
that the 2030 min for trace to form could be better used,
instructions were recently added for students to build molecular
models of fat and soap while waiting.
This experiment has been used very successfully in four
classes, with approximately 60 students (30 pairs) in 4 h
organic chemistry labs that are almost exclusively populated by
biology majors. However, the two parts of this lab, extraction
and soap making, could be easily separated into two, 2 h
sections to accommodate other lab schedules. A lab assessment
procedure indicated that students were able to conceptualize
the theory behind extraction and reapply the extraction
procedure during another, more open-ended experiment later
in the semester. Students reported signicant satisfaction with

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B

DOI: 10.1021/acs.jchemed.5b00188
J. Chem. Educ. XXXX, XXX, XXXXXX

Journal of Chemical Education

Communication

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DOI: 10.1021/acs.jchemed.5b00188
J. Chem. Educ. XXXX, XXX, XXXXXX